Steady-State and Time Resolved Fluorescence Analysis on Tyrosine–Histidine Model Compounds
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Four model compounds, for a tyrosine–histidine covalent bonding, 2-(5-imidazolyl)-4-methylphenol (C–C bonding in ortho-position at the phenyl group); 2′-(1-imidazolyl)-4-methylphenol (C–N bonding in ortho′-position at the phenyl group); 2-(5-imidazolyl)-4-H-phenol and 2-(5-imidazolyl)-4-H-phenol, at physiological pH have been studied by UV-Vis absorption, steady-state and time resolved fluorescence spectroscopy. Their absorption and emission properties are presented and discussed. The photophysical properties depend on the para-substituted phenyl group as well as on C–C/C–N bonding in the Phenol–Imidazole linkage. The N position, N1–N3/N1–N4, in the imidazole group was found to be relevant. The results are discussed with relevance to the redox processes of tyrosine and to better understand the role of a tyrosine–histidine covalent linkage as found in cytochrome c oxidase.
KeywordsTyrosine–histidine model compounds Cytochrome c oxidase UV absorbance Fluorescence lifetime
This work was supported by CNRS, ULP and ANR. M. Voicescu is grateful for financial support from the CNRS. The authors are indebted to Prof. van der Donk’s team, UIUC, Illinois, USA for Tyr–His model compounds synthesis.
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